US4110367A - Sulfonated alkylphenoxy acetones - Google Patents
Sulfonated alkylphenoxy acetones Download PDFInfo
- Publication number
- US4110367A US4110367A US05/654,068 US65406876A US4110367A US 4110367 A US4110367 A US 4110367A US 65406876 A US65406876 A US 65406876A US 4110367 A US4110367 A US 4110367A
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- US
- United States
- Prior art keywords
- dye
- acid
- dyeing
- sulfonated
- alkylphenoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical group CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Chemical group 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- WZEMSIKSCALWJZ-UHFFFAOYSA-N azane;ethanol Chemical group N.CCO.CCO WZEMSIKSCALWJZ-UHFFFAOYSA-N 0.000 claims 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical group CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 31
- 239000004753 textile Substances 0.000 abstract description 27
- 238000004043 dyeing Methods 0.000 abstract description 23
- 229920001778 nylon Polymers 0.000 abstract description 22
- 239000004677 Nylon Substances 0.000 abstract description 20
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 abstract description 13
- 239000000980 acid dye Substances 0.000 abstract description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 19
- 239000002253 acid Substances 0.000 description 11
- 239000004744 fabric Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 4
- -1 fatty alcohol sodium sulfates Chemical class 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000003839 salts Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- COKCGFHKHBCVRI-UHFFFAOYSA-N 3-phenoxypentadecan-2-one Chemical class CCCCCCCCCCCCC(C(C)=O)OC1=CC=CC=C1 COKCGFHKHBCVRI-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- KJWMCPYEODZESQ-UHFFFAOYSA-N 4-Dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C=C1 KJWMCPYEODZESQ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- DGOBMKYRQHEFGQ-UHFFFAOYSA-L acid green 5 Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=CC(=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 DGOBMKYRQHEFGQ-UHFFFAOYSA-L 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- FPVGTPBMTFTMRT-UHFFFAOYSA-L disodium;2-amino-5-[(4-sulfonatophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 235000019233 fast yellow AB Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- XQYMIMUDVJCMLU-UHFFFAOYSA-N phenoxyperoxybenzene Chemical compound C=1C=CC=CC=1OOOC1=CC=CC=C1 XQYMIMUDVJCMLU-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
-
- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C3/00—Tanning; Compositions for tanning
- C14C3/02—Chemical tanning
- C14C3/08—Chemical tanning by organic agents
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/62—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
- D06P1/621—Compounds without nitrogen
- D06P1/622—Sulfonic acids or their salts
- D06P1/625—Aromatic
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid dyes
Definitions
- This invention relates to sulfonated alkylphenoxy acetones, and to the use of these compounds as dye levelers in dyeing synthetic polyamide textiles with acid dyes to alleviate barre'.
- anionic surfactants have been employed as dye levelers in the dyeing of nylon textiles with acid dyes.
- One of the earliest class of anionic surfactants used were the mixed fatty alcohol sodium sulfates. Subsequently, alkyl sulfonate and alkyldiaryl sulfonate surfactants were recommended. More recently, more complex anionics have been alleged to prevent barre', for example: sulfonated sulphones derived from a variety of hydroxy-substituted aryl compounds in U.S. Pat. No. 3,536,438, dialkyl sulfosuccinates in U.S. Pat. No.
- R is an alkyl group having an average of 8-20 carbon atoms
- M is hydrogen, sodium, potassium, ammonium, or substituted ammonium
- n is a number of from 1 to 2 inclusive.
- the alkyl radical R in the invention compounds may be straight chained or branched, may be saturated or unsaturated, and may be comprised of a mixture of alkyl groups having differing numbers of carbon atoms. Because of its ready availability and low cost, invention compounds produced from dodecyl phenol are preferred.
- the substituent M in the invention compounds is hydrogen in the acid form of the compounds, or sodium, potassium, ammonium, or substituted ammonium (by which is meant watersoluble amines such as ethyl amine, dimethyl amine, diethanol amine and the like in the salt form).
- n is 1 or 2, or some fractional number between 1 and 2 when the invention compound comprises a mixture of the monosulfonated and disulfonated compounds, for example, 1.5 when equal parts of each are present. Best dye leveling has been obtained when n is 1.
- the invention compounds are readily prepared, as illustrated and described in more detail in the following examples, by first sulfonating a phenol having a para-substituted alkyl group having an average 8-20 carbon atoms with enough sulfonating agent (chlorosulfonic acid, oleum and the like) to give the desired average number of sulfonic acid groups.
- This reaction is well known, as shown for example in U.S. Pat. Nos. 2,249,757 and 3,707,352, and is most easily done in solution using an organic solvent inert to the reaction such as ethylene dichloride, 1,2-dichloropropane and the like.
- the resulting sulfonated intermediate is neutralized with an aqueous sodium or potassium hydroxide solution, and about a stoichiometric quantity of monochloroacetone added slowly over a period of 30-60 minutes. Additional aqueous sodium or potassium hydroxide is added concurrently with the chloroacetone to neutralize the HCl generated and at a rate that maintains the reaction at a pH of at least 8.
- the resulting phenoxy ether product which can be recovered and purified by conventional means, will be in the form of the salt of the alkali metal hydroxide used.
- the acid form is produced by reacting the salt with a suitable acid, such as HCl, and purifying and isolating by conventional means.
- ammonium hydroxide or a watersoluble amine is used in the synthesis in place of the sodium or potassium hydroxide.
- the acid form of the invention compound can be reacted with the desired ammonium compound.
- the invention compounds have been discovered to be effective dye levelers for nylon textiles dyed with acid dyes, being effective anti-barre' agents for a variety of nylon dye combinations.
- the nylon textiles, acid dyes, and dyeing procedures utilized are conventional.
- the nylon textiles to be dyed may be in the form of fibers (either staple or continuous), fabrics (woven, nonwoven, knitted and the like), or finished textile goods; and may consist of only synthetic polyamide, or may consist of blends of the polyamide with other textile materials (such as polyesters, polyacrylonitriles, wool, cotton, and the like) compatible with the dyes and the dyeing conditions used for the nylon.
- the acid dyes employed may be any of those normally used for dyeing nylon, as for example, those belonging to the azo, anthraquinone, quinophthalone, phthalocyanine or triphenylmethane classes of dyes or the nitro of formazane dyestuffs, which optionally may contain complex-bound metals, such as copper, nickel, chromium or cobalt.
- the quantity of the invention sulfonated alkylphenoxy acetone employed usually will be the minimum necessary to provide an acceptably uniform and streak-free dyed textile (dye-leveling quantity).
- acceptable alleviation of barre' can be achieved with about 0.25 to 4.0 parts by weight of the invention compound per 100 parts by weight of the nylon textile being dyed. In most cases, from about 0.5 to 1.0 part will be optimum from a cost/performance standpoint. Since the invention compound is facilely produced, marketed, and used in industrial dyeing as an aqueous dispersion, the salt, being most soluble, will normally be employed.
- the acid form of the invention compounds is equally suitable when its lesser solubility does not cause problems. Because of their lower costs, the alkali metal salts are normally preferred for dye leveling. While only one of the invention compounds is usually employed, mixtures of two or more may be used. Further, for some dyeings, other anionic surfactants may advantageously be used in conjunction with the invention compounds.
- the invention dyeleveler compounds like those of the prior art, normally, are most effective if added to the dye bath containing the nylon textile before the dye, and preconditioning the textile for some finite period, such as 5 to 30 minutes, before dye addition.
- Dyeing temperatures normally vary between 60° and 120° C., with 80°-100° C. being typical.
- temperatures of about 25°-60° C. are usual, followed by higher temperatures, such as 80°-120° C., after the dye addition.
- the bath typically is maintained at a pH of about 6 to 8, and is lowered to about 4.0 or less near the end of the cycle if more complete dye exhaust and improved washfastness is desired.
- a compound of the above formula is produced as follows: 256 parts (2.2 moles) of chlorosulfonic acid is added over two hours to an agitated solution of 272 parts of p-dodecylphenol (1 mole based on OH number) and 400 parts of ethylene dichloride maintained at 0°-25° C. The resulting mixture is agitated at 10°-25° C. for about six hours under a slight vacuum to remove HCl. Then, 1092 parts of 15% aqueous KOH (2.93 moles) is added with stirring while maintaining the temperature at 30°-50° C.
- Example 1 The sulfonated dodecylphenoxy acetone of Example 1 was evaluated as a dye leveler in a series of dye tests employing an Ahiba laboratory dyeing machine, 10-gram samples of a nylon tiger stripe test fabric, and the following dyestuffs:
- the dyeing procedure used for each test consisted of: preparing 300 mls of a dyebath containing 2% o.w.f. of ammonium sulfate and either 0.5% or 1.0% o.w.f. of the dye leveler, setting the bath at 120° F., entering the fabric sample and running ten minutes at 120° F., adding the dyestuff and running ten minutes at 120° F., raising the bath temperature about 2°/minute to 212° F. and running for 60 minutes more, adding to 0.5% o.w.f. of acetic acid and running for 30 minutes at 212° F., rinsing the fabric with warm water, spin-extracting the rinse water, and air drying the fabric.
- sulfonated alkylphenoxy acetones may also be employed in other applications where sulfonate-containing surfactants are used.
- sulfonate-containing surfactants may be used as detergents, dispersing agents, emulsifying agents for latex polymerizations, textile wetting agents, penetrating agents, leather tanning agents, textile scouring agents, and the like.
- the presence of a carbonyl group in the molecule can be advantageous because of its reactivity potential.
Abstract
The novel compounds, sulfonated alkylphenoxy acetones. In dyeing nylon textiles, with acid dyes, barre' is reduced by using these novel compounds as a dye leveler.
Description
This invention relates to sulfonated alkylphenoxy acetones, and to the use of these compounds as dye levelers in dyeing synthetic polyamide textiles with acid dyes to alleviate barre'.
In dyeing synthetic polyamide textiles such as fibers, fabrics, or garments (hereafter collectively called "nylons" or "nylon textiles") with acid dyes, there often is obtained barre' or streakiness in the dyed textile due to inherent physical and/or chemical differences existing in the yarns from which the textile has been made. For further information about the causes and manifestations of barre' reference is made to U.S. Pat. No. 3,619,122 and American Dyestuff Reporter, Feb. 12, 1968, pgs. 42-47.
To prevent or minimize barre' to an acceptable degree, a variety of anionic surfactants have been employed as dye levelers in the dyeing of nylon textiles with acid dyes. One of the earliest class of anionic surfactants used were the mixed fatty alcohol sodium sulfates. Subsequently, alkyl sulfonate and alkyldiaryl sulfonate surfactants were recommended. More recently, more complex anionics have been alleged to prevent barre', for example: sulfonated sulphones derived from a variety of hydroxy-substituted aryl compounds in U.S. Pat. No. 3,536,438, dialkyl sulfosuccinates in U.S. Pat. No. 3,619,122, alkane-or alkene-amido-benzene-sulphonics in U.S. Pat. No. 3,713,768, and monosulfonated alkylphenoxy glycerol in U.S. Pat. No. 3,809,717. Also, alkyl-substituted diphenyl ether sulfonates, believed to have the general formula shown in U.S. Pat. No. 3,127,441, have been used.
In spite of the abundance of work done to identify anionic surfactants capable of minimizing or preventing barre', a need still exists for new dye levelers considering the great number of different acid dyes employed, the fact that they are typically used in combinations, and the variety of nylon textiles being dyed. In many instances less-than-satisfactory barre' effects are tolerated because a dye leveler suitable from both an economic and a performance standpoint is unavailable.
Considering this state of the art, it is an object of the present invention to provide new anoinic surfactants that function as dye levelers and are effective in minimizing or preventing barre' effects when used in the dyeing of a variety of nylon textiles with different acid dyes.
This object and other objects and advantages, which will become apparent from the following description and examples, are provided by the novel sulfonated alkylphenoxy acetones hereinafter described, and by their utilization in dyeing nylon textiles with acid dyes.
The new sulfonated alkylphenoxy acetones that it has been discovered funtion as dye levelers in dyeing nylons with acid dyes have the general formula: ##STR1## wherein:
R is an alkyl group having an average of 8-20 carbon atoms;
M is hydrogen, sodium, potassium, ammonium, or substituted ammonium; and
n is a number of from 1 to 2 inclusive.
The alkyl radical R in the invention compounds may be straight chained or branched, may be saturated or unsaturated, and may be comprised of a mixture of alkyl groups having differing numbers of carbon atoms. Because of its ready availability and low cost, invention compounds produced from dodecyl phenol are preferred.
The substituent M in the invention compounds is hydrogen in the acid form of the compounds, or sodium, potassium, ammonium, or substituted ammonium (by which is meant watersoluble amines such as ethyl amine, dimethyl amine, diethanol amine and the like in the salt form).
Lastly, in the invention compounds n is 1 or 2, or some fractional number between 1 and 2 when the invention compound comprises a mixture of the monosulfonated and disulfonated compounds, for example, 1.5 when equal parts of each are present. Best dye leveling has been obtained when n is 1.
The invention compounds are readily prepared, as illustrated and described in more detail in the following examples, by first sulfonating a phenol having a para-substituted alkyl group having an average 8-20 carbon atoms with enough sulfonating agent (chlorosulfonic acid, oleum and the like) to give the desired average number of sulfonic acid groups. This reaction is well known, as shown for example in U.S. Pat. Nos. 2,249,757 and 3,707,352, and is most easily done in solution using an organic solvent inert to the reaction such as ethylene dichloride, 1,2-dichloropropane and the like. The resulting sulfonated intermediate is neutralized with an aqueous sodium or potassium hydroxide solution, and about a stoichiometric quantity of monochloroacetone added slowly over a period of 30-60 minutes. Additional aqueous sodium or potassium hydroxide is added concurrently with the chloroacetone to neutralize the HCl generated and at a rate that maintains the reaction at a pH of at least 8. The resulting phenoxy ether product, which can be recovered and purified by conventional means, will be in the form of the salt of the alkali metal hydroxide used. The acid form is produced by reacting the salt with a suitable acid, such as HCl, and purifying and isolating by conventional means. When the ammonium or substituted ammonium salt is desired, ammonium hydroxide or a watersoluble amine is used in the synthesis in place of the sodium or potassium hydroxide. Alternatively, the acid form of the invention compound can be reacted with the desired ammonium compound. The synthesis of sulfonated alkylphenoxy compounds by procedures similar to that described herein are disclosed in U.S. Pat. Nos. 2,178,830, 3,707,352 and 3,809,717.
As previously described, the invention compounds have been discovered to be effective dye levelers for nylon textiles dyed with acid dyes, being effective anti-barre' agents for a variety of nylon dye combinations. Generally, the nylon textiles, acid dyes, and dyeing procedures utilized are conventional.
Thus, the nylon textiles to be dyed may be in the form of fibers (either staple or continuous), fabrics (woven, nonwoven, knitted and the like), or finished textile goods; and may consist of only synthetic polyamide, or may consist of blends of the polyamide with other textile materials (such as polyesters, polyacrylonitriles, wool, cotton, and the like) compatible with the dyes and the dyeing conditions used for the nylon.
The acid dyes employed, generally, may be any of those normally used for dyeing nylon, as for example, those belonging to the azo, anthraquinone, quinophthalone, phthalocyanine or triphenylmethane classes of dyes or the nitro of formazane dyestuffs, which optionally may contain complex-bound metals, such as copper, nickel, chromium or cobalt.
The quantity of the invention sulfonated alkylphenoxy acetone employed usually will be the minimum necessary to provide an acceptably uniform and streak-free dyed textile (dye-leveling quantity). Generally, depending on a number of interrelated factors, such as type of nylon, type and quantity of the dye, dyeing conditions and the like, acceptable alleviation of barre' can be achieved with about 0.25 to 4.0 parts by weight of the invention compound per 100 parts by weight of the nylon textile being dyed. In most cases, from about 0.5 to 1.0 part will be optimum from a cost/performance standpoint. Since the invention compound is facilely produced, marketed, and used in industrial dyeing as an aqueous dispersion, the salt, being most soluble, will normally be employed. The acid form of the invention compounds, however, is equally suitable when its lesser solubility does not cause problems. Because of their lower costs, the alkali metal salts are normally preferred for dye leveling. While only one of the invention compounds is usually employed, mixtures of two or more may be used. Further, for some dyeings, other anionic surfactants may advantageously be used in conjunction with the invention compounds.
With respect to the dyeing process, the invention dyeleveler compounds like those of the prior art, normally, are most effective if added to the dye bath containing the nylon textile before the dye, and preconditioning the textile for some finite period, such as 5 to 30 minutes, before dye addition. Dyeing temperatures normally vary between 60° and 120° C., with 80°-100° C. being typical. When the textile is preconditioned, temperatures of about 25°-60° C. are usual, followed by higher temperatures, such as 80°-120° C., after the dye addition. During dyeing, the bath typically is maintained at a pH of about 6 to 8, and is lowered to about 4.0 or less near the end of the cycle if more complete dye exhaust and improved washfastness is desired. Control of pH is usually achieved with compounds such as acetic acid, formic acid, dilute sulfuric or phosphoric acid, ammonium sulfate, sodium acetate and the like. Other materials often used in acid dyeing may also be used with the invention compounds, as for example: nonionic surfactants to improve fabric wetting or control the degree of dye dispersion; organic water-miscible solvents, such as isopropanol, to predisperse the acid dyes or assist in fabric wetting; and chelating agents, such as ethylenediamine tetra-acetic acid, to tie up iron and other polyvalent metal ions that can adversely effect the dyeing process or product quality. After dyeing, the nylon textile is normally washed with water before being dried.
A compound of the above formula is produced as follows: 256 parts (2.2 moles) of chlorosulfonic acid is added over two hours to an agitated solution of 272 parts of p-dodecylphenol (1 mole based on OH number) and 400 parts of ethylene dichloride maintained at 0°-25° C. The resulting mixture is agitated at 10°-25° C. for about six hours under a slight vacuum to remove HCl. Then, 1092 parts of 15% aqueous KOH (2.93 moles) is added with stirring while maintaining the temperature at 30°-50° C. Next, 548 parts of 15% aqueous KOH (1.47 moles) and 92 parts of monochloroacetone acid (1 mole) are concurrently added to the stirred reaction mixture within a 30 minute period while maintaining the temperature at 68°-72° C., care being taken to add the KOH at a rate sufficient to maintain the reaction mixture at a pH of 8 or more (measured on a 5% solution). The reaction mixture is refluxed (70°-75° C.) for six hours with vigorous agitation, cooled, and allowed to stand for 16 hours at 40°-50° C. The reaction mixture divides into two layers and the top aqueous layer is discarded. 800 parts of water are added to the bottom organic layer and its pH adjusted to 9 ± 0.5 using either 10% HCl or 15% KOH. All of the ethylene dichloride is azeotropically distilled off and the batch cooled. Lastly, 200 parts of isopropanol is admixed in and the pH adjusted to 9 ± 0.5. The product is storage stable and usable as a leveling agent in dyeing nylon textiles.
The sulfonated dodecylphenoxy acetone of Example 1 was evaluated as a dye leveler in a series of dye tests employing an Ahiba laboratory dyeing machine, 10-gram samples of a nylon tiger stripe test fabric, and the following dyestuffs:
______________________________________ BROWN DYE 0.8% o.w.f. Acid Blue #232 0.25% o.w.f. Acid Yellow #49 0.05% o.w.f. Acid Red #99 0.05% o.w.f. Acid Bule #247 BLUE DYE 0.25% o.w.f. Acid Blue #122 GREEN DYE 0.25% o.w.f. Acid Green #25 ______________________________________
The dyeing procedure used for each test consisted of: preparing 300 mls of a dyebath containing 2% o.w.f. of ammonium sulfate and either 0.5% or 1.0% o.w.f. of the dye leveler, setting the bath at 120° F., entering the fabric sample and running ten minutes at 120° F., adding the dyestuff and running ten minutes at 120° F., raising the bath temperature about 2°/minute to 212° F. and running for 60 minutes more, adding to 0.5% o.w.f. of acetic acid and running for 30 minutes at 212° F., rinsing the fabric with warm water, spin-extracting the rinse water, and air drying the fabric.
The results of the dye-leveling tests are compiled in the Table. In the tests, the improvement in color uniformity (alleviation of barre') over a blank (no dye leveler) was ascertained independently for each dyestuff. Color uniformity ratings were based on an arbitrary scale of 1-5, with 1 being the poorest and 5 the best. The color uniformity ratings shown in the Table are the average of five ratings by different textile chemists. From this data it can be seen that the invention compound of Example 1 functions as a dye leveler in dyeing a nylon textile with a variety of acid dyes. For some dyes and nylon textiles, better leveling may be achieved with invention compounds having only one sulfonate group.
______________________________________ Dye Color Example 1 Blank ______________________________________ Brown 0.5% o.w.f. 2.8 1.0 1.0% o.w.f. 3.2 Blue 0.5% o.w.f. 2.4 1.0 1.0% o.w.f. 2.9 Green 0.5% o.w.f. 2.5 1.0 1.0% o.w.f. 3.4 ______________________________________
The invention sulfonated alkylphenoxy acetones may also be employed in other applications where sulfonate-containing surfactants are used. For example, they may be used as detergents, dispersing agents, emulsifying agents for latex polymerizations, textile wetting agents, penetrating agents, leather tanning agents, textile scouring agents, and the like. For some of these applications, the presence of a carbonyl group in the molecule can be advantageous because of its reactivity potential.
Claims (5)
1. A compound having the formula ##STR3## wherein: R is an alkyl group having 8-20 carbon atoms;
M is hydrogen, sodium, potassium, ammonium, ethyl ammonium, dimethyl ammonium, or diethanol ammonium; and
n is a number of from 1 to 2 inclusive.
2. The compound of claim 1 wherein n is 1.
3. The compound of claim 1 wherein R is an alkyl group having 12 carbon atoms.
4. The comound of claim 3 wherein M is potassium or sodium.
5. The compound of claim 4 wherein n is 1.
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US05/654,068 US4110367A (en) | 1976-02-02 | 1976-02-02 | Sulfonated alkylphenoxy acetones |
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US05/654,068 US4110367A (en) | 1976-02-02 | 1976-02-02 | Sulfonated alkylphenoxy acetones |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0347373A1 (en) * | 1988-06-06 | 1989-12-20 | Ciba-Geigy Ag | Aqueous solutions of synthetic tanning agents |
US20040172773A1 (en) * | 2003-01-13 | 2004-09-09 | Kang Peter K. | Selective application of chemical agents in the pattern dyeing of textiles |
CN100365194C (en) * | 2003-01-13 | 2008-01-30 | 美利肯公司 | Selective application of chemical agents in the pattern dyeing of textiles |
Citations (3)
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US2178829A (en) * | 1938-02-07 | 1939-11-07 | Rohm & Haas | Condensation products |
US3766254A (en) * | 1970-05-05 | 1973-10-16 | Chevron Res | Linear alkylphenol disulfonate phosphate free detergent actives |
US3809717A (en) * | 1971-04-05 | 1974-05-07 | Basf Ag | Sulfonated phenol ethers |
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1976
- 1976-02-02 US US05/654,068 patent/US4110367A/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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US2178829A (en) * | 1938-02-07 | 1939-11-07 | Rohm & Haas | Condensation products |
US3766254A (en) * | 1970-05-05 | 1973-10-16 | Chevron Res | Linear alkylphenol disulfonate phosphate free detergent actives |
US3809717A (en) * | 1971-04-05 | 1974-05-07 | Basf Ag | Sulfonated phenol ethers |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0347373A1 (en) * | 1988-06-06 | 1989-12-20 | Ciba-Geigy Ag | Aqueous solutions of synthetic tanning agents |
US20040172773A1 (en) * | 2003-01-13 | 2004-09-09 | Kang Peter K. | Selective application of chemical agents in the pattern dyeing of textiles |
WO2004063459A3 (en) * | 2003-01-13 | 2005-03-24 | Milliken & Co | Selective application of chemical agents in the pattern dyeing of textiles |
US7014665B2 (en) * | 2003-01-13 | 2006-03-21 | Milliken & Company | Selective application of chemical agents in the pattern dyeing of textiles |
CN100365194C (en) * | 2003-01-13 | 2008-01-30 | 美利肯公司 | Selective application of chemical agents in the pattern dyeing of textiles |
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